1,2-Bis(dibromomethyl)benzene supplier

Name
ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE
EINECS 236-176-2
CAS No. 13209-15-9
Article Data13
CAS DataBase
Density 2.392 g/cm³
Solubility Insoluble in water
Melting Point 114-116 ºC
Formula C₈H₆Br₄
Boiling Point 343.9 °C at 760 mmHg
Molecular Weight 421.752
Flash Point 157.8 °C
Transport Information UN 3261
Appearance off-white to grey crystalline powder
Safety 26-36/37/39-45
Risk Codes 34-36/37-20/21/22
Molecular Structure
Hazard Symbols C
Synonyms o-Xylene, a,a,a',a'-tetrabromo- (6CI,8CI);1,2-Bis(dibromomethyl)benzene;NSC 38607;a,a,a',a'-Tetrabromo-o-xylene;
PSA 0.00000
LogP 5.26340

Synthetic route

: 95-47-6
o-xylene

A: 13209-15-9
1,2-bis(dibromomethyl)benzene

B: 95110-95-5
1-(dibromomethyl)-2-(tribromomethyl)benzene

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 19h; Irradiation;	A 72% B 6%
With N-Bromosuccinimide for 19h;	A 38% B 42%

: 95110-95-5
1-(dibromomethyl)-2-(tribromomethyl)benzene

: 13209-15-9
1,2-bis(dibromomethyl)benzene

Conditions

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃;	40%

: 95-47-6
o-xylene

: 13209-15-9
1,2-bis(dibromomethyl)benzene

Conditions

Conditions	Yield
With bromine at 120 - 170℃; Irradiation;
With bromine at 140℃;
With bromine im Sonnenlicht;

: 552-45-4
1-chloromethyl-2-methylbenzene

: 13209-15-9
1,2-bis(dibromomethyl)benzene

Conditions

Conditions	Yield
With bromine at 140 - 160℃; Irradiation;

: 7726-95-6
bromine

: 552-45-4
1-chloromethyl-2-methylbenzene

A: 13209-15-9
1,2-bis(dibromomethyl)benzene

B 2-chlorobromomethyl-1-dibromomethyl-benzene: 2-chlorobromomethyl-1-dibromomethyl-benzene

Conditions

Conditions	Yield
at 140 - 160℃; Irradiation;

...Expand

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 764-42-1
1,2-Dicyanoethylene

: 22856-30-0
2,3-dicyanonaphthalene

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 75 - 80℃; for 8h;	97%
With sodium iodide In N,N-dimethyl-formamide at 75℃; for 7h;	88%
With sodium iodide In N,N-dimethyl-formamide at 75℃; for 5.5h;	78%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: phenylmagnesium bromide

: 713-36-0
2-benzyltoluene

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation; Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution; Stage #3: With water Substitution;	92%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: phenylmagnesium bromide

: 716-78-9
1-benzyl-2-(deuteriomethyl)benzene

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation; Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution; Stage #3: With water-d2 Substitution;	92%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
Stage #1: 1,2-bis(dibromomethyl)benzene With sulfuric acid Stage #2: With water; sodium hydrogencarbonate Product distribution / selectivity;	91%
With sulfuric acid Product distribution / selectivity;	79%
With sulfuric acid

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 106-51-4
p-benzoquinone

: 3029-32-1
6,13-pentacenequinone

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 120℃;	91%
With sodium iodide In N,N-dimethyl-formamide at 120℃; Inert atmosphere;	91%
Stage #1: p-benzoquinone With sodium iodide In N,N-dimethyl-formamide at 70℃; Inert atmosphere; Stage #2: 1,2-bis(dibromomethyl)benzene In N,N-dimethyl-formamide at 70℃; for 18h; Diels-Alder Cycloaddition; Inert atmosphere;	28%

: 338989-51-8
7-methoxy-1H-inden-1-one

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1345090-10-9
1-methoxy-11H-benzo[b]fluoren-11-one

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 24h;	90%

: 108-31-6
maleic anhydride

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 716-39-2
2,3-Naphthalenedicarboxylic anhydride

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	87.6%
With sodium iodide In N,N-dimethyl-formamide at 70℃; for 4.5h; Diels-Alder Cycloaddition;	50%

: 4453-90-1
1,4-dihydro-1,4-methanonaphthalene

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 107426-42-6
C19H14

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	87%

: (4,4'-di-tert-butyl-2,2'-bipyridine)dimethylplatinum(II)

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1359769-65-5
trans-[PtMe2(CHBr-o-C6H4CHBr2)Br(4,4'-di-tert-butyl-2,2'-bipyridine)]

Conditions

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.16 mmol) added to soln. of Pt complex (0.16 mmol); stirred (4 h); evapd. (vac.); recrystd. from CH2Cl2/Et2O; elem. anal.;	87%

: 541-59-3
maleiimide

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 4379-54-8
2,3-Naphthalimide

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 70 - 80℃; for 10h;	86%

: 39103-38-3, 74719-73-6
(E)-2-styrylchromone

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 2-(3-phenylnaphth-2-yl)chromone

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide for 16h;	86%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 100-52-7
benzaldehyde

: 1730-25-2
allylmagnesium bromide

: 2-[2-(3-butenyl)phenyl]-1-phenylethanol

Conditions

Conditions	Yield
Stage #1: allylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation; Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution; Stage #3: benzaldehyde Substitution;	85%

...Expand

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 81402-06-4
6-(hydroxymethyl)naphthalene-1,4-dione

: 1005001-34-2
2-(hydroxymethyl)-5,12-naphthacenequinone

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 80℃;	85%

: 52594-52-2
dimethyl(2,2'-bipyridine)platinum(II)

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1359769-63-3
[PtMe2(CHBr-o-C6H4CHBr2)Br(2,2'-bipyridine)]

Conditions

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.14 mmol) added to soln. of Pt complex (0.14 mmol); stirred (24 h); evapd. (vac.); solidified with CH2Cl2/Et2O; elem. anal.;	85%

: 52594-55-5
[(1,10-phenanthroline)dimethylplatinum(II)]

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1359769-64-4
[PtMe2(CHBr-o-C6H4CHBr2)Br(1,10-phenanthroline)]

Conditions

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.25 mmol) added to soln. of Pt complex (0.25 mmol); stirred (24 h); evapd. (vac.); solidified with CH2Cl2/Et2O; elem. anal.;	85%

: 2973-09-3
n-butylmaleimide

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 128600-23-7
N-Butyl-β-naphthalimide

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 85℃; for 12h; Diels-Alder Cycloaddition; Schlenk technique; Inert atmosphere;	85%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 149-73-5
trimethyl orthoformate

: 37864-64-5
phthalic aldehyde bis(dimethyl)acetal

Conditions

Conditions	Yield
With zinc(II) chloride at 90℃; for 5h;	85%
With zinc(II) chloride at 90℃; for 5h;	85%

: 55977-30-5, 133567-73-4
2-[(1E)-2-(4-chlorophenyl)ethenyl]-4H-1-benzopyran-4-one

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 2-[3-(4-chlorophenyl)naphth-2-yl]chromone

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide for 16h;	83%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 154968-64-6
9,10-Diacetoxy-1,4,5,8-tetrahydro-1,4:5,8-dimethanoanthracene

: 288625-16-1
7,16-diacetoxy-(6α,8α,15α,17α)-6,8,15,17-tetrahydro-6,17:8,15-dimethanoheptacene

Conditions

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 20 - 55℃; for 5.5h;	83%

: 52594-52-2
dimethyl(2,2'-bipyridine)platinum(II)

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1359769-66-6
[Pt2Me4Br2(μ-o-(CHBr)2C6H4)(2,2'-bipyridine)2]

Conditions

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.13 mmol) added to soln. of Pt complex (0.26 mmol); stirred (4 h); evapd. (vac.); recrystd. from CHCl3/hexane; elem. anal.;	80%

: 52594-55-5
[(1,10-phenanthroline)dimethylplatinum(II)]

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1359884-75-5
[Pt2Me4Br2(μ-o-(CHBr)2C6H4)(1,10-phenanthroline)2]

Conditions

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.12 mmol) added to soln. of Pt complex (0.25 mmol); stirred (4 h); evapd. (vac.); recrystd. from CHCl3/hexane; elem. anal.;	80%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 107426-40-4
C18H22

: 107426-41-5
DN-6

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	79%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 189133-04-8
5,12-Diacetoxy-1,4,7,10-tetrahydro-1,4:7,10-dimethanonaphthacene

: 7,18-diacetoxy-(6α,9α,16α,19α)-6,9,16,19-tetrahydro-6,19:9,16-dimethanooctacene

Conditions

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 20 - 55℃; for 5.5h;	79%

: 498-66-8
norborn-2-ene

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 32058-86-9
C15H14

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	78%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 83602-18-0
(1α,4α,4aβ,5α,8α,8aβ)-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene

: 107426-37-9
C28H22

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	75%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 180134-63-8
((1R,4S,5R,8S)-10-Ethoxycarbonylmethoxy-1,4,5,8-tetrahydro-1,4;5,8-dimethano-anthracen-9-yloxy)-acetic acid ethyl ester

: 699018-43-4
C40H34O6

Conditions

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 55℃; under 75.006 Torr; for 6h;	75%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 6,13-dihydro-6,13-methanopentacene

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 24h;	75%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 117157-38-7
6,7-dibromonaphthalene-1,4-dione

: 2,3-dibromo-5,12-tetracenequinone

Conditions

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide at 110℃; for 48h; Inert atmosphere; Sealed tube;	75%
With sodium iodide In N,N-dimethyl acetamide at 90℃; for 24h;	72%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 107426-39-1
C23H16

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	74%

: 7213-65-2
5,8-diacetoxy-1,4-dihydro-1,4-methylenonaphthalene

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 1233126-07-2
1,4-diacetoxy-5,12-dihydro-5,12-methylenotetracene

Conditions

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 20 - 55℃; under 75.0075 Torr; Diels-Alder reaction;	74%

1,2-Bis(dibromomethyl)benzene Specification

The IUPAC name of this product is 1,2-bis(dibromomethyl)benzene . With the CAS registry number 13209-15-9, it is also named as NSC 38607 ; alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene ; o-Xylene, alpha,alpha,alpha',alpha'-tetrabromo- ; Benzene, 1,2-bis(dibromomethyl)- ; alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene .

The 1,2-Bis(dibromomethyl)benzene is off-white to grey crystalline powder. It is insoluble in water. It can cause burns. And it is irritating to eyes and respiratory system. Harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

The 1,2-Bis(dibromomethyl)benzene can be obtained by 1-dibromomethyl-2-tribromomethyl-benzene with Pd(OAc)₂, PPh₃and Et₃N in the solvent dimethylformamide . The recation temperature is 100 °C and the yield is 40%.

The 1,2-Bis(dibromomethyl)benzene is used in the preparation of other chemicals. For example: 1. It can reacts with 5endo,6endo-Bis-chlormethyl-norborn-2-en to get trans/cis-2,3-bis(chloromethyl)-1,4-methano-1,2,3,4-tetrahydroanthracene ; 2. It also can reacts with allylmagnesium bromide to obtain 1-(3-butenyl)-2-(deuteriomethyl)benzene ; 3. It reacts with exo-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene to obtain exo-benzocyclobuteno-1,2,3,4-tetrahydro-1,4-methanoanthracene .

The other characteristics of this product can be summarized as: (1)ACD/BCF (pH 5.5): 4628.7 ; (2)ACD/BCF (pH 7.4): 4628.7 ; (3)ACD/KOC (pH 5.5): 14632.84 ; (4)ACD/KOC (pH 7.4): 14632.84 ; (5)#Freely Rotating Bonds: 2 ; (6)Index of Refraction: 1.685 ; (7)Molar Refractivity: 67.01 cm³ ; (8)Molar Volume: 176.2 cm³ ; (9)Polarizability: 26.56×10^-24 cm³ ; (10)Surface Tension: 58.1 dyne/cm ; (11)Enthalpy of Vaporization: 56.45 kJ/mol ; (12)Vapour Pressure: 0.000136 mmHg at 25°C. People can use the following data to convert to the molecule structure. SMILES: BrC(Br)c1ccccc1C(Br)Br; InChI: InChI=1/C8H6Br4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,7-8H.

Product Name

ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE

Synthetic route

1,2-Bis(dibromomethyl)benzene Specification

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